[N-(2-pyrimidine oxy) benzylamino phenyl] sulfamine compound, and its preparing method and use

A kind of technology of benzylaminophenyl and sulfonamide, applied in the field of new [N-benzylaminophenyl]sulfonamide compounds

Inactive Publication Date: 2006-03-08
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although pyrimidine salicylates have high herbicidal activity, they are currently only suitable for weed control in cotton fields and rice fields

Method used

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  • [N-(2-pyrimidine oxy) benzylamino phenyl] sulfamine compound, and its preparing method and use
  • [N-(2-pyrimidine oxy) benzylamino phenyl] sulfamine compound, and its preparing method and use
  • [N-(2-pyrimidine oxy) benzylamino phenyl] sulfamine compound, and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthesis of [N-(2-pyrimidinyloxy)benzylaminophenyl]sulfonamides

[0050] Take I-4 synthesis as an example:

[0051] The first step: sulfonylation: Add (5mmol) saturated potassium carbonate solution, 221.5mg (1.0mmol) p-nitrobenzenesulfonyl chloride and 123mg (1.0mmol) o-methoxyaniline to a three-necked flask with a 100mL dropping funnel, and heat to 60-70°C, stir for about 2 hours after the addition, and filter the filter cake to obtain 292 mg of 4-nitrobenzenesulfonyl (2'-methoxy)aniline, with a yield of 95%.

[0052] The second step: nitro reduction: dissolve 292mg of 4-nitrobenzenesulfonyl (2'-methoxy)aniline in 20mL of anhydrous methanol, add 30mg (equivalent to 4-nitrobenzenesulfonyl (2'-methyl The mass of oxy)aniline (10%) Raney Ni, 100mg (1.5mmol) of 80% hydrazine hydrate was added dropwise to the reaction solution, stirred at room temperature until the reaction was complete, and the end point of the reaction was controlled by TLC. After filtration, the filtra...

Embodiment 2

[0066] The synthesis of I-1, the detailed experimental procedure is the same as that of Example 1: (1) Sulfonylation: the feeding amount is 6 mmol of n-butylamine, and the product is 1.4 g, and the yield is 90%. (2) Nitro reduction: the amount of sulfonylated product is 6 mmol, which is spin-dried and put into the next step directly, with a yield of 99%. (3) Condensation with salicylaldehyde: the amount of feed is 6mmol amino, spin-dried and directly enter the next step, the yield is 99%. (4) Schiff base reduction: the amount of imine was 6 mmol, and 1.82 g (5.44 mmol) of the product was obtained, with a yield of 90%. (5) Condensation with 4,6-dimethoxy-2-thiamphenicol pyrimidine: using acetonitrile as a solvent, synthesized at 40-50°C, the amount of feed is 1.82 grams (5.44mmol) of imine reduction products, column layer Analysis (petroleum ether: ethyl acetate = 3:1) yielded a pure product with a yield of 95%.

[0067] solid

[0068] m.p.: 132.2+0.5°C

[0069] 1 H NMR (3...

Embodiment 3

[0076] The synthesis of I-2, the detailed experimental procedure is the same as that of Example 1: (1) Sulfonylation: the feeding amount is 6 mmol of di-n-butylamine, and the product is 1.82 g, and the yield is 97%. (2) Nitro group reduction: the feeding amount is 6 mmol of the sulfonylated product. In this step, when filtering RaneyNi, it needs to be washed several times with chloroform, and the yield is 99%. (3) Condensation with salicylaldehyde: the amount of feed is 6mmol amino, spin-dried and directly enter the next step, the yield is 99%. (4) Schiff base reduction: the amount of imine was 6 mmol, and 2.214 g (5.671 mmol) of the product were obtained, with a yield of 95%. (5) Condensation with 4,6-dimethoxy-2-thiamphenicol pyrimidine: using acetonitrile as a solvent, synthesized at 40-50°C, the amount of feed is 2.214 grams (5.671mmol) of imine reduction products, column layer Analysis (petroleum ether: ethyl acetate = 2:1) yielded a pure product with a yield of 87%.

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Abstract

This invention relates to a group of compounds [N-(2-pyrimidinyloxy) benzyl amino phenyl] sulfonamide. In the general formula as shown right, D or E = C1~C4 alkoxyl or C1~C4 halogenated alkyloxyl; X= H, halogens, nitro, C1~C8 alkyl, C1~C8 halogenated alkyl and C1~C8 alkyloxyl; R1, R2= H, halogens, nitro, phenyl, halogenated or C1~C4 alkyl-substituted phenyl or heterocyclic radical which includes pyridyl, thienyl, thiazyl and pyrimidinyl.

Description

technical field [0001] The present invention relates to a new class of [N-(2-pyrimidinyloxy)benzylaminophenyl]sulfonamide compounds, a preparation method and use as an agricultural chemical herbicide. Background technique [0002] Pesticides are an indispensable means of production for human beings to obtain food and ensure stable and high yields in agriculture. In the past century, pesticides such as insecticides, fungicides, and herbicides have made great contributions to human beings. In recent years, with the continuous growth of the world population, human beings' demand for food is also increasing, but the growth rate of cultivated land is far behind the speed of population growth. To solve this worldwide problem, we must rely on increasing the food production per unit area. To increase yield and improve crop quality, various means must be adopted, such as breeding, cultivation, fertilization, etc., and the application of pesticides is also one of the indispensable mea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/34A01N43/54
Inventor 吕龙陈杰唐庆红吕强徐小燕金志平景竹黄玉
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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